Di-tert-butylphenol compounds are a class of compounds known for their use as stabilizers for plastics, oils and fats; see, e.g., U.S. Pat. No. 3,711,544 issued to Engelhardt, Fruhstorfer, Hesse, Dennler & Baumer on Jan. 16, 1973.
Certain di-tert-butylphenol compounds and other compounds structurally related thereto have been found to have significant anti-inflammatory and/or analgesic activity. Such compounds, processes for making them, and uses for them are disclosed in the following references: U.S. Pat. Nos. 3,784,701 issued to Tomcufcik, Grassing & Sloboda on Jan. 8, 1974; 3,917,672 issued to Schmidt on Nov. 4, 1975; 4,124,725 issued to Moore on Nov. 7, 1978; 4,130,666 issued to Moore on Dec. 19, 1978; 4,165,383 issued to Moore on Aug. 21, 1979; 4,172,082 issued to Moore on Oct. 23, 1979; 4,357,345 issued to Moore on Nov. 2, 1982; 4,418,074 issued to Moore on Nov. 29, 1983; 4,440,784 issued to Katsumi, Kondo, Yamashita, Hidaka, Hosoe, Ariki, Yamashita & Watanobe on Apr. 3, 1984; 4,535,165 issued to Moore on Aug. 13, 1985; 4,677,113 issued to Bell & Moore on Jun. 30, 1987; 4,708,966 issued to Loomans, Matthews & Miller on Nov. 24, 1987; 4,714,776 issued to Bell & Moore on Dec. 22, 1987; 4,833,155 issued to Muchowski, Greenhouse, Young & Murthy on May 23, 1989; 4,968,710 issued to Rustad on Nov. 6, 1990; 4,982,006 issued to Hudec on Jan. 1, 1991; 5,086,064 issued to Capris, Conner & Sircar on Feb. 4, 1992; 5,102,897 issued to Boschelli, Conner, Kostlan, Kramer, Mullican & Sircar on Apr. 7 1992; European Patent Application No. 0,212,848 of Riker Laboratories, published Mar. 4, 1987; PCT Patent Application Nos. WO 83/01774 and WO 83/91775 of Riker Laboratories, both published May 26, 1983; WO 93/07865 of The Procter & Gamble Company, published Apr. 29, 1993; Kaffenberger, R. M., T. H. Eichhold & M. J. Doyle, "Determination of Tebufelone (A New Anti-inflammatory Drug) Strength and Stability in Bulk Drug, Dosage Formulations and Feed Admixtures by Reversed-Phase High-Performance Liquid Chromatography", Journal of Chromatofiraphy, Vol. 505 (1990), pp. 349-356. Such compounds are also disclosed and reviewed in Bart, D. G., "5-Lipoxygenase Inhibitors and Their Anti-inflammatory Activities", Progress in Medicinal Chemistry, Vol. 29 (1992), pp. 1-15, 45-50, and references disclosed therein.
Although a number of di-tert-butylphenol compounds have been demonstrated to exhibit anti-inflammatory activity, many such compounds exhibit little or no anti-inflammatory activity. Thus it is generally not possible to predict whether such compounds have substantial anti-inflammatory activity without testing for the activity.
It is an object of the subject invention to provide compounds which have effective anti-inflammatory, analgesic and/or anti-oxidant activity.
It is a further object of the subject invention to provide such compounds which cause few adverse side effects.
It is also an object of the subject invention to provide methods for treating inflammation and/or pain using the subject compounds.